Two late goals for Wycombe saw Southend let a 3-1 lead slip to lose 4-3 at Adams Park and remain without a point this season.
Blues had gotten off to the perfect start in beautiful sunshine when Brandon Goodship’s first-time strike beat Ryan Allsop for the striker’s first goal in a Southend shirt.
Stephen Humphrys then doubled Blues’ lead in superb fashion, arching a brilliant strike from over 20-yards past the despairing dive of Allsop to make it 2-0.
That lead would be halved before the break when Mark Milligan put into his own net but Southend’s two-goal lead would be restored when Humphrys scored again straight after the restart.
Scott Kashket ensured a nervy finish by scoring with over half-an-hour to go while Southend’s goal frame was struck three times as Wycombe aimed to salvage their unbeaten league start.
And the Chairboys would grab a late equaliser as Wycombe flooded forward and defender Anthony Stewart scored in the 89th minute with it looking like the points would be shared.
But the comeback was completed in the second minute of stoppage time as Kashket ducked one way and then another before curling the ball beyond Bishop to win it for the Chairboys.
After letting a two-goal lead slip twice, it was a bitter pill to swallow for Southend who had looked deserving of at least a point on their travels but their wait to get off the mark goes on.
Despite suffering four straight defeats going into this afternoon’s trip to Adams Park, Southend boss Kevin Bond had remained upbeat after the defeat to Peterborough United in midweek.
As a result, Bond refused to make wholesale changes at Wycombe with Simon Cox making way for Stephen Humphrys and his faith was rewarded as the visitors got off to a perfect start.
A break from Blues ended with Ethan Hamilton weaving his way into the penalty area before teeing up Brandon Goodship whose first-time strike beat goalkeeper Ryan Allsop to give Southend the lead.
Goodship’s first of the season had the travelling Southend fans rocking in the away end with just nine minutes on the clock and had Blues in front for the first time in the league this season.
And Southend fans would be in dreamland as Blues grabbed a second on the half-hour mark with a superbly taken goal from Humphrys doubling Blues’ lead.
The masked striker brought the ball forward with menace before cutting onto his left foot and curling a beautiful effort from 25-yards beyond the dive of Allsop to make it 2-0 to the visitors.
All Bond and his staff would have wanted now was for Southend to make it to the interval without conceding but they weren’t able to manage it with one of their own netting for Wycombe.
With Scott Kashket causing all sorts of problems along the edge of the penalty area, Mark Milligan came back to help his defenders only to prod the ball past Bishop and reduce the arrears.
Blues would have been wary coming out for the second-half of a Wycombe response to going in 2-1 down, but Southend responded in the best way possible by restoring their two-goal advantage.
Less than two minutes after the restart, Humphrys was faced up by Darius Charles and with no other option available the striker decided to have a go at goal and brilliantly found the bottom corner.
Although Humphrys’ second of the game had given Southend daylight, scoring so early in the half meant there was still plenty of time for the home side to respond, and respond they did.
Substitute David Wheeler’s attempted strike from outside the box fell kindly at the feet of Kashket who calmly slotted the ball past Bishop and reduce Southend’s lead with over half-an-hour to go.
The home side had the wind in their sails following Kashket’s goal and Blues were fortunate not to concede an equaliser as the Chairboys hit the woodwork twice in a matter of seconds.
The crossbar was first to be struck when Wheeler’s header crashed off the bar before Dominic Gape went just as close with a long-range strike which came flying back off the post.
Southend’s goal was living a charmed life as Kashket would strike the woodwork for a third time with less than 10 minutes remaining as Blues desperately tried holding on.
Last time Southend lost their opening four games of a season they would go on to win their fifth and finish 12th in the old Division Three, and it looked like history was about to repeat itself here.
That was until Wycombe stunned the visitors with two goals in three minutes to complete a barely believable turnaround and condemn Southend to a fifth straight league defeat.
The Chairboys would level matters with a minute of normal time remaining as Adebayo Akinfenwa teed up Anthony Stewart who fired through a crowded penalty area to find the bottom corner.
And in the second minute of five added on, the comeback was complete as Kashket got himself inside the box before having to poise to fire past Bishop.
Wycombe Wanderers XI: Allsop, Grimmer, Jacobson, Stewart, Charles, Gape, Bloomfield (C), Pattison (Akinfenwa 55’), Kashket, Onyedinma (Wheeler 45’), Samuel (Freeman 78’). Subs Not Used: Yates, Mascoll, Phillips, Parker
Blues XI: Bishop, Bwomono (Blackman 89’), Ralph, Milligan (C), Humphrys (Robinson 71’), Goodship (Ndukwu 60’), Hamilton, Mantom, Shaughnessy, Lennon, White. Subs Not Used: Oxley, Hyam, Cox, Kiernan
Referee: Darren Drysdale
Assistants: Ollie Williams & Leigh Crowhurst
Fourth Official: Mike Desborough
Wycombe Wanderers: Mark Milligan O.G. 35’, Scott Kashket 55’, 90+2’, Anthony Stewart 89’
Southend United: Brandon Goodship 11’, Stephen Humphrys 30’, 47’
Wycombe Wanderers: None
Southend United: Harry Lennon 43’, Nathan Bishop 75’